2-azido-4-benzylamino-4N,3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranosyl trichloroacetimidate | 1258284-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-azido-4-benzylamino-4N,3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranosyl trichloroacetimidate
• CAS: 1258284-50-2
• 化学式: C₁₆H₁₆Cl₃N₅O₄
• 分子量: 448.693
• InChiKey: LZNFCWZJQWOTNK-KABOQKQYSA-N

反应信息

• 作为反应物：
  描述：

  2-azido-4-benzylamino-4N,3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranosyl trichloroacetimidate 、 methyl 2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-galactopyranosyl-(1→3)-2,4-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到methyl 2-azido-4-benzylamino-4-N,3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-galactopyranosyl-(1→3)-2,4-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a trisaccharide repeat of the zwitterionic Sp1 capsular polysaccharide utilizing 2-azido-4-benzylamino-4N,3-O-carbonyl-2,4,6-trideoxy-d-galactopyranosyl trichloroacetimidate

  摘要：

  2-Azido-4-benzylamino-4N,3-O-carbonyl-2,4,6-trideoxy-D-galactopyranosyl trichloroacetimidate 2 conveniently prepared in six steps from 6-deoxy-D-glucal glycosylated a selectively protected alpha 1,3 linked methyl galabioside to afford the trisaccharide skeleton of a repeating unit of the Sp1 zwitterionic capsular polysaccharide. Lithium hydroxide hydrolysis of the 3,4-cyclic carbamate permitted the creation of a 2-acetamido-4-amino-2,4,6-trideoxygalactose residue. Selective cleavage of p-methoxybenzyl ethers by trifluoroacetic acid gave a selectively deprotected trisaccharide with two hydroxymethyl groups that were oxidized by the TEMPO reagent to afford access to trisaccharide glycoside 1 containing 2-acetamido- 4-amino-2,4,6-trideoxygalactose and two galacturonic acid residues. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2013.05.005